The addition of nucleophiles to electron-deficient alkenes represents one of the more general and commonly used strategies for the convergent assembly of more complex structures from simple precursors. In this review the addition of diverse protic and organometallic nucleophiles to electron-deficient alkenes followed by enantioselective protonation is summarized. Reactions are first categorized by the type of electron-deficient alkene and then are further classified according to whether catalysis is achieved with chiral Lewis acids, organocatalysts, or transition metals.

Mentions:
In one of the early examples of conjugate addition–enantioselective protonation, Shibasaki and co-workers demonstrated that chiral lanthanum and samarium tris(BINOL) complexes (Fig. 3), developed by the Shibasaki group for asymmetric Michael additions using malonates and organometallic reagents, are effective catalysts for the sequential conjugate addition of 4-tert-butyl(thiophenol) to α,β-unsaturated thioesters followed by enantioselective protonation (Scheme 33) [61].

Mentions:
In one of the early examples of conjugate addition–enantioselective protonation, Shibasaki and co-workers demonstrated that chiral lanthanum and samarium tris(BINOL) complexes (Fig. 3), developed by the Shibasaki group for asymmetric Michael additions using malonates and organometallic reagents, are effective catalysts for the sequential conjugate addition of 4-tert-butyl(thiophenol) to α,β-unsaturated thioesters followed by enantioselective protonation (Scheme 33) [61].

The addition of nucleophiles to electron-deficient alkenes represents one of the more general and commonly used strategies for the convergent assembly of more complex structures from simple precursors. In this review the addition of diverse protic and organometallic nucleophiles to electron-deficient alkenes followed by enantioselective protonation is summarized. Reactions are first categorized by the type of electron-deficient alkene and then are further classified according to whether catalysis is achieved with chiral Lewis acids, organocatalysts, or transition metals.